16 Celebrity Couples You Never Knew Dated
Do you remember these couples?! Can you believe Mila Kunis and Macaulay Culkin dated for nearly a decade?
Celebrity relationships tend to come and go pretty quickly, so unless you’re keeping up with your favorite idol, you’ve likely forgotten about most stars’ romantic pasts. But it’s fun to reminiscence about former duos, especially when they’ve completely escaped your memory — and feel pretty surprising now.
Here are some of our favorite celebrity couples you probably forgot about.
1. Madonna & Tupac Shakur
In 2015, Madonna admitted that she had dated Tupac in the early ’90s. The revelation made headlines. She even revealed that he had inspired her infamous, profanity-filled 1994 appearance on David Letterman.
Earlier this year, TMZ released a letter Tupac had written from jail to the famous songstress, expressing his sorrow about their breakup.
2. Sandra Bullock & Ryan Gosling
Although Sandra Bullock may have been 16 years older than Ryan Gosling, that didn’t stop the two from dating in 2002.
The two famous actors met after working together on the set of Murder By Numbers. However, their romance didn’t last long, after which he went on to date Rachel McAdams.
3. Ashton Kutcher & January Jones
It’s hard to picture Ashton Kutcher with anyone other than his wife Mila Kunis, but at point, he had a romance with actress January Jones.
Kutcher was January Jones’s first boyfriend when she came to Los Angeles, but it sounds like her memories of him aren’t very fond. She told GQ magazine that he wasn’t supportive of her acting. Luckily, she still found success without him.
4. Madonna & Dennis Rodman
Madonna sure had her fair share of famous romances. In addition to Tupac, Madonna also had a short tryst with Dennis Rodman.
5. Cher & Tom Cruise
It seems that the age gap doesn’t mean much in Hollywood. Although she was 39 at the time, Cher was completely smitten for 23-year-old Tom Cruise back in the ’80s.
It seems wild to picture now, but they were once a happy couple. Cher has even called Tom Cruise one of her top five favorite former lovers.
6. Ciara & Bow Wow
Ciara and Bow Wow did more than just collaborate on their 2005 song “Like You” — they also got together in real life. They met when they were 17 and Ciara was an extra in his tour.
Although they only dated for two years, they’re reportedly still close to this day.
7. Emily Blunt & Michael Bublé
This handsome couple dated for three years back in the late 2000s.
Although they may look picture perfect, it doesn’t look like things ended well between the two. There are rumors that Bublé cheated on the actress, although Blunt has chosen not to speak about the topic.
8. Britney Spears & Colin Farrell
Although no one has ever forgotten Britney Spears and Justin Timberlake, most people don’t seem to remember that the pop star dated Colin Farrell back in 2003.
The pair was surprising given Spears’ wholesome image and Farrell’s bad boy reputation. Although their romance was short, sources close to the pop star speculate that Britney saw Colin as the one who got away.
9. Mila Kunis & Macaulay Culkin
Before she settled down with Ashton Kutcher, Mila Kunis had a serious relationship with “Home Alone” star Macaulay Culkin.
Kunis has discussed how hard it was to date Culkin, since he was such a big celebrity at the time. Despite his crazed fans, they had a relationship for eight years until they split in 2011. It seems there is no bad blood, however, as Culkin recently congratulated Kunis on the birth of her baby.
10. Wilmer Valderrama & Lindsay Lohan
Wilmer Valderrama is known for dating younger ladies — and not just his more recent girlfriend, Demi Lovato. Valderrama was also romantic with Lindsay Lohan.
The two dated in 2004 when she was 17, and he was 24. The two kept their relationship quiet, however, until Lohan was 18.
11. Kim Kardashian & Nick Cannon
Before she was the megastar that she is today, Kim Kardashian dated Nick Cannon from 2006 to 2007.
However, according to Cannon, he broke up with her when he found out she lied about her infamous tape with Ray J. Cannon recently shared some throwback photos from their relationship, some of which include hangouts with other celebs like Paris Hilton and Lil’ Kim.
12. Sheryl Crow & Owen Wilson
Sheryl Crow and Owen Wilson dated from 1997-2000 after they met on the set of “The Minus Man.” From the looks of it, the duo wasn’t quite compatible, as the competition got too fierce.
Crow spoke of her past relationships and said: “I have always gone out with guys who were highly successful, which would seem like it would put me at an equal level. But what ends up happening is that one of you becomes smaller — and it was always me.”
13. Gwyneth Paltrow & Brad Pitt
Back in the 90’s Gwyneth Paltrow and Brad Pitt were the ultimate power couple. They were even engaged!
After meeting on the set of “Seven,” they dated for nearly three years before calling it quits. Luckily, there’s no bad blood, and they two are reportedly still friendly.
14. John Mayer & Jennifer Aniston
John Mayer has had his fair share of famous girlfriends, and Jennifer Aniston was no exception.
15. Hilary Duff & Joel Madden
Although she was just a 16-year-old Disney starlet and he was a 25-year-old rockstar, Hillary Duff and Joel Madden dated for a few years back in the 2000s.
Despite the age difference, Duff called Madden “The most respectful boyfriend she has ever had.” She even said it took five or six dates before they ever kissed.
16. Nicky Hilton & Kevin Connolly
Nicky Hilton and “Entourage” star Kevin Connolly dated on and off for several years back in the early 2000s.
Although Hilton was already well-known as an heiress, the two began dating when Connolly was a struggling actor. According to Connolly, their relationship was nothing but normal. “We watch ‘Desperate Housewives’ and fall asleep,” he told PEOPLE in 2005.